A bacterial quorum-sensing signaling molecule
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N-cis-hexadec-9Z-enoyl-L-Homoserine lactone

Item No. 10012673

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(2S,9Z)-tetrahydro-2-oxo-3-furanyl]-9-hexadecenamide
CAS Number
479050-94-7
Synonyms
  • C16:1-Δ9-(L)-HSL
  • N-(2-oxotetrahydrofuran-3S-yl) Palmitoleyl Amide
Molecular Formula
C20H35NO3
Formula Weight
337.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
SMILES
CCCCCC/C=C\CCCCCCCC(=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C20H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)21-18-16-17-24-20(18)23/h7-8,18H,2-6,9-17H2,1H3,(H,21,22)/b8-7-/t18-/m0/s1
InChi Key
BDQHAQLGRDSHKW-ZEVQVBBLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density.1 This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.2 Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group) and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family.3 N-cis-hexadec-9Z-enoyl-L-Homoserine lactone is a long-chain AHL that functions as a quorum sensing signaling molecule in strains of S. meliloti.4,5,6,7 Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therapy in the treatment of infectious diseases.8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol. Mol. Biol. Rev. 70(4), 859-875 (2006).

    2. Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J. Bacteriol. 188(2), 773-783 (2006).

    3. Penalver, C.G.N., Morin, D., Cantet, F., et al. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions. FEBS Lett. 580(2), 561-567 (2006).

    4. Teplitski, M., Eberhard, A., Gronquist, M.R., et al. Chemical identification of N-acyl homoserine lactone quorum-sensing signals produced by Sinorhizobium meliloti strains in defined medium. Arch. Microbiol. 180(6), 494-497 (2003).

    5. Gao, M., Chen, H., Eberhard, A., et al. sinI- and expR-dependent quorum sensing in Sinorhizobium meliloti. J. Bacteriol. 187(23), 7931-7944 (2005).

    6. Marketon, M.M., Glenn, S.A., Eberhard, A., et al. Quorum sensing controls exopolysaccharide production in Sinorhizobium meliloti. J. Bacteriol. 185(1), 325-331 (2003).

    7. Marketon, M., Gronquist, M.R., Eberhard, A., et al. Characterization of the Sinorhizobium meliloti sinR/sinI locus and the production of novel N-Acyl homoserine lactones. J. Bacteriol. 184(20), 5686-5695 (2002).

    8. Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies. Nat. Rev. Microbiol. 6(1), 17-27 (2008).